STEREOCHEMISTRY .81. MICHAEL REACTIONS OF ALLYLIC SULFONES WITH NITROOLEFINS - REGIOCHEMICAL AND STEREOCHEMICAL CONTROL

被引：8

作者：

GHERA, E

BENYAAKOV, E

YECHEZKEL, T

HASSNER, A

机构：

[1] Department of Chemistry, Bar-Ilan University Ramat Gan

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 19期

关键词：

MICHAEL REACTIONS; ALLYLIC ANIONS; SULFONES; NITROOLEFINS;

D O I：

10.1016/S0040-4039(00)79071-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Michael addition of allylsulfone carbanions to nitroolefins where shown to be sensitive to substitution in both the donor and the acceptor. While sulfone 10 gave predominantly products of gamma-addition with aromatic nitroolefins, addition to aliphatic nitroolefins produced almost exclusively alpha-adducts. In the presence of an OH function in the sulfone (see 13) only (Z) gamma-adducts were observed, while a bromine substituent reversed the regiochemistry.

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页码：2741 / 2744

页数：4

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